The Red Sox have made no secret of their desire to make a push for Jon Lester, a notion that has gained further credence with the reports (the first one of which came from ESPNBoston.com) that the team has made an offer to the left-hander.

But, of course, it is one thing to make an offer, another to find common ground to satisfy Lester’s interest in a salary befitting his status as an elite pitcher and the Sox’ interests in accounting for the risks associated with a long-term deal for a pitcher in his 30s. In the absence of concrete details about what shape that offer has taken, here are a few potential models and/or features of an offer that the Sox may try to incorporate as they attempt to reacquire an elite pitcher while minimizing the risk on the back end of the deal:

Model 1: Cliff Lee (fewer years, more dollars)

In the 2012-13 offseason, the Red Sox proved aggressive in terms of the average annual value they put on the table while trying to limit the number of years they committed to players. In doing so, they got (for instance) Shane Victorino to pass on a four-year deal worth roughly $11 million a year from the Indians in favor of a three-year, $39 million deal to come to Boston.

In the winter following the 2010 season, left-hander Cliff Lee walked away from potential deals of six-plus years (with offers typically rumored to be for $23 million or so per year) in favor of a five-year, $120 million deal ($24 million per year) with the Phillies. It’s worth noting that there are similarities between Lester’s situation and Lee’s.

By Alex Speier | Comments Off on Cliff Lee’s precedent for an improbable shoot-the-moon scenario for Jon Lester, Red Sox

ST. PETERSBURG, Fla. — Jon Lester saw no reason to dismiss the idea. Get traded by the Red Sox in July, then re-sign with the club four months down the line?

“Why not?” he said in the Red Sox clubhouse after a 6-4 defeat to the Rays. “This is what I know. This is what I love.”

The idea of a player getting dealt only to turn around and re-sign as a free agent is unusual — but not unprecedented. In 1993, Rickey Henderson was sent by the A’s to the Blue Jays for Steve Karsay; Henderson helped the Jays to the second of back-to-back World Series wins, then turned around and re-signed with Oakland that offseason. In 1995, the Twins traded closer Rick Aguilera to the Red Sox for Frankie Rodriguez in July; that winter, Aguilera re-signed with Minnesota.

Yet another example of a more recent ilk may be more in line with a best-case scenario for the Red Sox and Lester. After the 2009 season, the Phillies sent left-hander Cliff Lee to the Mariners as part of a three-team deal that landed Roy Halladay in Philadelphia. One year later, teams were coming at Lee with six- and even seven-year offers. Yet even with the Yankees seemingly willing to open up the vault for Lee, the left-hander decided to return to the Phillies on a five-year, $120 million deal. Read the rest of this entry »

Yahoo! Sports baseball reporter Jeff Passan joined Dennis & Callahan on Friday morning, and after calling the Jake Peavy acquisition ‘stabilizing,’ Passan was very, very high on the Red Sox‘ potential successes ‘ both in the short term and long term.

‘A lot of it depends on what happens with Clay Buchholz,’ Passan said of the Sox’ chances this season in particular. ‘If they can come out with a rotation of Buchholz, [Jon] Lester, [John] Lackey and Peavy in some order or fashion there, that’s pretty good, especially if a guy like Drake Britton can step up along with a guy like MattThornton as their lefty specialist, and if Koji Uehara can continue the masterful pitching he’s showed.

“I hope people there recognize how damn good that guy has been. It’s not the prettiest thing in the world, but he throws as many strikes as anybody and is somehow striking out guys like Craig Kimbrel this year. It’s a beautiful thing to watch. ‘¦ And you can’t say anything bad about the hitting. That lineup can be absolutely devastating. [Jacoby] Ellsbury is earning himself a nine-figure contract with his season. [Shane] Victorino has been stable in the two-hole. [Dustin] Pedroia is Pedroia. [David] Ortiz is like an ageless man.’

Passan also expects Xander Bogaerts to come up and take over as the starting third baseman within the next month. The fact that the Red Sox held on to him and the rest of their top prospects at the trade deadline puts them in an envious position for the foreseeable future.

‘What the Red Sox have right now, they’re on the cusp ‘ remember things back in 2004, and not just because of the World Series, but because of the young players, [the Red Sox] got really, really exciting there?’ Passan said. ‘That’s happening again. Not all these guys will turn out well. ‘¦ They have so much inventory in the mid- to upper-level minors that the Red Sox have a chance to be devastatingly good the next five years if they play their cards right.’

Part of that comes as a result of the Red Sox not trading for Cliff Lee, who would have come at a hefty cost in terms of both dollars and prospects. As far as Passan knows, discussions between the Phillies and Red Sox about Lee never got very far.

Lee wasn’t the only Philadelphia pitcher in the conversation, though.

Passan didn’t mince words when it came to Jonathan Papelbon, the Phillies closer who made news over the weekend for publicly criticizing, well, the entire organization that gave him a four-year, $50 million contract in November 2011.

‘That’s like a prom date that ends up looking like ‘Carrie,’ ‘ Passan said, referencing the Stephen King novel and subsequent movie by the same name. ‘It’s really, really ugly there. You guys know Jonathan Papelbon, did you expect anything less? He’s an infant, and he always has been. He happens to be an infant who can pitch very well, but he’s running into that lovely phenomenon that all of us do called aging. And he’s losing juice on his fastball and turning around and blaming others for what he feels like is a bad situation that he has plenty to do with.’

With the dust settling following Wednesday’s non-waiver trade deadline, Red Sox general manager Ben Cherington joined Dennis & Callahan Thursday morning, saying that even though the team made only one acquisition ‘ that of Jake Peavy ‘ his phone was much, much busier.

‘Any starting pitcher that was moved at the deadline, or was even potentially available, we talked about,’ Cherington said. ‘But I think the issue is really ‘ we really felt for a variety of reasons that Peavy was the best fit: the combination of what we gave up, the control we have over him next year and our comfort with him as a person and how he fits into the rotation and clubhouse and all those things. That’s what we were most focused on.’

Cherington explained that there were a number of factors that permanently shifted the team’s focus from Phillies ace Cliff Lee to Peavy, including Lee’s big contract and Philadelphia’s large asking price. Also making a difference was that Lee was scratched from his start last weekend.

Despite Peavy’s injury history, the Red Sox aren’t worried about his ability to pitch down the stretch. He couldn’t say the same about Lee.

‘When you’re making a deal in July, it’s a little bit about next year, but it’s a lot about this year,’ Cherington said. ‘You want to make a trade for players who are going to walk in, be active and help your team from Day 1. If there’s any question about that whatsoever, even if it looks like a guy is going to be fine, it’s a hard thing to do. Peavy’s last two outings we’ve been at, we’ve seen him, he’s pitched, he looks healthy, he looks strong. He’ll step right into the rotation and help us this weekend.’

No matter who Cherington was after, the organization stuck to its philosophy of valuing and keeping its top prospects, particularly Xander Bogaerts and Jackie Bradley Jr. He would not go as far to say that they were untouchable, but he did give further indication of just how much the team expects the pair to play a significant role in future years.

‘I don’t think you say, ‘never, never, never’ to anything, but obviously the more convicted you are of a player and more important that player is to you long-term, the higher the bar is,’ Cherington said. ‘In talking about trading, the truth is we never got anywhere near considering them in a deal this July. There wasn’t one presented that would have made sense. But I don’t think you say ‘never, never.’ Who knows what comes down the pipe?’

Lee, who is 10-4 with a 3.05 ERA, is signed through 2015 and set to make around $70 million over the next two seasons. Heyman’s report indicated that a team would need to pay for all of Lee’s $70 million as well as give up at least two top prospects.

‘¢ With Peavy already dealt and Lee’s asking price likely too high for most teams, Bud Norris of the Astros becomes one of the most interesting pitchers to watch as the deadline approaches. Yahoo! Sports reporter Jeff Passan reported that Norris is very likely to be dealt before Wednesday’s 4 p.m. deadline, and that Pittsburgh appears to be the likely landing spot. Brian T. Smith of the Houston Chronicle agreed, tweeting ‘all signs pointing toward Norris being traded before the deadline.’

‘¢ It looks as if the Cubs will be trading another outfielder, but it is yet to be seen which one they will deal between Nate Schierholtz and David DeJesus. Ken Rosenthal of Fox Sports reported that the Pirates are the most likely location for either player, but that DeJesus is the more likely to be moved. A player like Schierholtz would be more likely to be moved than Cubs relievers Kevin Greggor James Russell,according toESPN’s Jayson Stark.

Schierholtz, who is under team control for 2014 as an arbitration-eligible player, is batting .272 with 14 home runs and 43 RBIs. DeJesus, who is 33 years old and has a club option for 2014, is batting .268 with six homers and 24 RBIs.

The Cubs won’t trade Jeff Samardzija at the deadline, according toHeyman. Chicago reportedly was looking for a package of top-tier prospects for the 28-year-old starter, but they now will wait until the winter to try to sign him to a long-term contract or trade him. Samardzija is 6-9 with a 3.75 ERA.

‘¢ The Athletics, who also were reported to be going after Peavy, announced a trade of their own Tuesday night, when they sent Grant Green to the Angels in return for Alberto Callaspo. Callaspo, who has played second and third base in his career, likely will be playing mostly second for the Athletics. He is batting .252/.324/.347 with five homers and 36 RBIs.

The Red Sox have been reported to be the most likely candidate to land Cliff Lee, but trading for Lee will take several top prospects, according to Olney.

‘I think they are willing to trade him if someone gives them exactly what they want,’ Olney said. ‘I don’t think that they are necessarily that motivated. I think someone has to give them a home run deal. Does that include [Xander] Bogaerts? Does that include Bogaerts-plus? Other guys? Either way you’re talking about a guy who is guaranteed a little more than $30 million a year for each of the next two years because of the buyout. It doesn’t figure that way, the payout doesn’t, but that is what his average annual value is for the next two years. That is crazy money. That is an extraordinary sum of money.

‘People around baseball ‘ the way that the sport is going, they are looking at recent examples with the Giants trading for Carlos Beltran put Zach Wheeler in the deal and now the Mets are sitting there with one of the best young pitchers in baseball in Zach Wheeler. People look at that and say, ‘Boy, was that a mistake.’ Last year when the Angels traded for Zach Greinke and Jean Segura was in the deal and now the Brewers have one of the best young shortstops in baseball and the Angels don’t have anything to show for that deal. Recent history will tell executives that you don’t trade your best prospects anymore because the sport is veering toward younger, cheaper players, and that is why I would be shocked if the Red Sox gave up someone like Bogaerts.’

Another top-tier starting pitcher that the Red Sox reportedly are after is Jake Peavy, who was scratched from his planned start Tuesday. Olney said that the White Sox are not satisfied with any of the offers they have received for Peavy yet.

‘I think the White Sox are going to trade him,’ Olney said. ‘I know some of the executives who have spoken with the White Sox are convinced that they are going to trade him between now and the deadline. Friends of Peavy are saying that he wants to go and that he wants a chance to win someplace.

‘They called some of the teams involved yesterday and said ‘ because they weren’t satisfied with the offers, and I can’t tell you exactly what their request to the Red Sox was ‘ but they basically said to the teams that, ‘Look, we are fully prepared to go on with Jake Peavy. We will build around Jake Peavy.’ And the teams on the other side were saying, ‘Yeah, OK.’ They are not buying that poker move, and I still think right now it comes down to Oakland vs. the Red Sox.”

Peavy, who has been the subject of trade rumors related to the Red Sox, Athletics, Braves, Cardinals and Orioles, brought five suitcases with him on the team’s road trip to Cleveland. However, these rumors appeared to cool off Monday, when the Athletics and Red Sox — the two favorites to acquire Peavy — reportedly moved on because the asking price was too high.

Peavy is 8-4 with a 4.28 ERA in 13 starts this year. The 32-year-old, who won the 2007 NL Cy Young Award with the Padres, is under contract through the 2014 season.

Boston was pegged as the most likely destination for Phillies left-hander Cliff Lee, who likely will be dealt, according to Andy Martino of the New York Daily News. A deal for Lee, who is 10-4 with a 3.05 ERA this season, would cost three or four top prospects, according to Jon Heyman of CBS, and it is unlikely that the Phillies would pay for any of the remaining $70 million on Lee’s contract. Salisbury also reported that Michael Young is drawing significant interest from the Red Sox and Yankees. The righty-hitting third baseman is batting .277 with a .342 on-base percentage and seven home runs.

‘¢ The Red Sox have shown interest in Rockies reliever Josh Outman, according to Troy E. Renck of The Denver Post. The Indians also are interested in the left-handed reliever, according to the report. Outman is 2-0 with a 4.42 ERA this season.

‘¢ The Cubs already have dealt Matt Garza, Alfonso Soriano, Scott Feldman and Scott Hariston, but they could continue to be active as the trade deadline approaches. Nate Schierholtz, who is batting .274 with 14 home runs, could be the next to leave town, according to Jesse Rogers of ESPNChicago.com. The Rangers have been one team to show interest in Schierholtz, according to the report. Jeff Samardzija has drawn several offers, but the asking price for him is very high, according to Heyman. Samardzija is 6-9 with a 3.75 ERA.

‘¢ Jason Kubel and Ian Kennedy could be on their way out of Arizona, according to Peter Gammons of MLB.com, as the two have struggled this year. However, the money saved by dealing Kubel and Kennedy is not expected to free up enough money for the Diamondbacks to get Peavy. Kubel is batting .234 with only five home runs, while Kennedy is 3-7 with a 5.22 ERA.

According to major league sources, the Red Sox remain engaged on pitchers Jake Peavy and Cliff Lee, as well as infielder Michael Young. But as of early Tuesday morning the team was not close to acquiring any of the players due to the continued high asking prices.

The Phillies and White Sox continue to ask for top-tier prospects for Lee and Peavy, respectively, while the Red Sox remain committed to not surrendering key pieces of their farm system.

One source said that of the two pitchers, Peavy would most likely be a more realistic acquisition for the Red Sox, although the 32-year-old’s price tag remains heftier than Boston is comfortable with.

Both Lee and Peavy are signed beyond this season, with the White Sox hurler due to earn $14.5 million in 2014, and the 34-year-old Phillies lefty making $25 million over the next two seasons with a $27.5 million vesting option for ’16.

Young — who is a free agent after this season — remains a prime target for the Red Sox, with the 36-year-old potentially filling the Sox’ need to upgrade offensively at third base. The organization also values Young’s reputation as a strong clubhouse presence.

Along with Young, the team’s biggest priority is identifying right-handed pitching help in its bullpen. Red Sox relievers have the worst batting average against in the American League when facing righty hitters. There is a thinking in the organization that even if a starter isn’t acquired, Brandon Workman can capably fill out the rotation until Clay Buchholz returns.

Ken Rosenthal joined Dennis & Callahan on Tuesday morning, and the Fox Sports baseball reporter, before chiming in on a handful of Red Sox-related issues, offered insight on the ongoing Biogenesis performance-enhancing drug issue and the expected suspensions for a number of players, including Alex Rodriguez and Ryan Braun.

‘There will be bombshells. The question is the timing,’ Rosenthal said. ‘Baseball cannot rush into this. They have to have everything in order. And whether that takes two more days or two more weeks ‘ or two more months, for that matter, which I doubt ‘ remains to be seen.

‘Just from yesterday, I didn’t get the sense that it was imminent in talking to some people. But who knows? What’s complicated about this is baseball can’t miss. They have to have everything in order before they announce the suspensions, then make sure the suspensions are solid enough that when they’re appealed ‘ and they will be appealed ‘ they hold up.’

Rosenthal went on to explain that these punishments will be due to ‘just cause,’ not traditional suspensions under the joint drug agreement ‘ 50 games for a first positive test of a banned substance, 100 games for a second positive test and a lifetime ban for a third.

As such, MLB needs to make sure it has its ducks in a row. Since the case has been so public ‘ due solely to leaks ‘ the suspensions will be announced before the appeals are heard, as opposed to after an appeal, as is usually the case for a positive test.

‘Baseball has to prove just cause,’ Rosenthal said. ‘It’s not a positive test. They have to make a case for just cause, and will they have it? We’ll see.’

ESPN baseball reporter Buster Olney joined Mut & Merloni on Wednesday, with the Red Sox having bounced back from their mid-May slump and back in first place in the American League East.

Olney said the Red Sox deserve their ranking as one of the best teams in baseball, while the Yankees might be headed for a dip after leading the division for a couple of weeks.

“I do, and I think they’re getting better,” he said of the Sox. “They have a nice baseline with that offense. Because it looks like all year, no matter what happens to the pitching staff, they’re going to be a team that scores runs. On the other hand, I’ve spent the last couple of days around the Yankees. And it feels like they have been this great marathoner, a group that went out early, and they’re starting to sputter a little bit. Some of the guys who have been so terrific for them early in the year are starting to fade.

“What I’m going to be fascinated by in the days ahead — because it looks like Kevin Youkilis is going to play this weekend and come back, it looks like Mark Teixeira is going to come back — is how does this change the culture of what they’ve been accomplishing? Because every day, Joe Girardi, the manager, has walked into his office and been able to — because he’s got so many pieces and parts he’s been working with, castoffs and players like that — on a daily basis, all he needs to focus on is picking the best lineup for that day. Well, now that Teixeira is coming back — I’m not saying he’s a bad player, but he’s going to play every day. Youkilis is going to play every day. So, Girardi is going to be fashioning his lineup in a very different way than he has been.

“And I just thought back to what happened to the Dodgers last year. They got off to a 34-14 start, [Don] Mattingly using all these pieces and parts. And they’re feeling was, hey, once we get [Matt] Kemp back, then that’s when we can get rolling. But what happened was, once they got those injured everyday guys back, they really fell apart. Because there was something about the esprit de corps that had just — it was an important part of what they were doing. And I think that’s what the case is with the Yankees. So, I’m going to be fascinated to see how Joe handles that lineup going forward.”

The Red Sox are heading to Philadelphia for a pair of games against the Phillies, who are underachieving for the second straight season. This has led to speculation that Philadelphia might considering trading one of its premier pitchers, ace left-hander Cliff Lee or closer Jonathan Papelbon. Olney explained why that’s unlikely.

“The Phillies, their owner, David Montgomery, is very conservative. He also is very cognizant of the idea that he’s got a lot of people who bought tickets to see his team play,” Olney said. “He will not necessarily be someone who’s going to be looking in July to blow it up and start over — even though it might make some sense, because Lee, after the next three years of his contract, he’s got a huge buyout of like $10½ million. He’s basically a $28 million-a-year pitcher. If you’re the Phillies, you might think it would make sense to get out from underneath that.

“But their ownership, as I mentioned, is not necessarily a group that would do that. And on top of that, and this is why I keep telling people, look, don’t go to sleep on the Phillies: They have two of the three worst teams in baseball in their division in the Mets and the Miami Marlins. And that’s why I think they’re going to hang around and hang around. We saw it at the end of last year, they made a run at the wild card spot, even though we all thought they stunk for most of the year. So, I don’t think that they’re going to trade Cliff Lee, I don’t think they’re going to trade Papelbon.”